A range of acrylic polymers incorporating azafulleroids and aziridinofullerenes
have been prepared. This was achieved through the synthesis of 3-bromopropyl acrylate.
which was subsequently copolymerised with other acrylic monomers. Nucleophilic
substitution of the bromine atom using sodium azide afforded the corresponding azido
substituted acrylic copolymer. The azido group is capable of forming a triazoline
derivative with [60]fullerene, which after extrusion of nitrogen, leads to the formation of
iminofullerene monoadducts attached to the acrylic polymer backbone.
Various fulleropyrrolidine monoadducts have been prepared by [3+2]
cycloaddition of azomethine ylides to [60]fullerene through use ofN-substituted and
unsubstituted a-amino acids in conjunction with benzaldehyde derivatives.
Fulleropyrrolidine and azafulleroid acrylic monomers have been prepared. The
fulleropyrrolidine monomer was formed by the creation of an amide bond between
acryloyl chloride and the pyrrolidine ring nitrogen of 2-phenylfulleropyrrolidine. For the
azafulleroid acrylic monomer an acrylic azide was reacted directly with [60] fullerene.
An investigation of the conditions required to polymerise the above monomers has been
carried out using a variety of cationic initiators.
An investigation into the reaction of an acid chloride containing polymer with 2-
phenylfulleropyrrolidine in a similar fashion to the formation of the acrylic
fulleropyrrolidine monomer above has also been performed. This has lead to the
formation of various soluble fullerene/acrylic polymers.
Various synthetic routes were investigated in order to form a fullerene
functionalised with an alcohol group. It was hoped that such an alcoholic fullerene might
provide a useful precursor to an acrylic monomer. While attempting to form an alcoholic
fullerene it was found that (5,6)-open 3-iminofulleropropyl benzoate forms three products
on addition of a molar ratio of a methanolic sodium hydroxide solution in sunlight.
Similar products are absent in the same reaction with (6,6)-open 3-iminofulleropropyl
benzoate. The relatively rapid formation of such well-defined products in the presence of
sodium hydroxide is intriguing. Characterisation of these products is also included in this
study.